Versatile synthesis of 11-oxabicyclo[4.4.1]undeca-1,5-dienes by selective epoxidation of 1,6-disubstituted (E,Z,E)-1,3,5-hexatrienes and subsequent cope rearrangement

Journal of Organic Chemistry

Volumn 64, Issue 11, 1999, Pages 3806-3812

  Von Zezschwitz, Paultheo ^a   Voigt, Katharina ^a   Lansky, Annegret ^a   Noltemeyer, Mathias ^a   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

11 OXABICYCLO[4.4.1]UNDECA 1,5 DIENE; ALKADIENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; EPOXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033612391     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981496u     Document Type: Article

References (60)

1. (a) de Meijere, A.; Bräse, S. J. Organomet. Chem. 1999, in press.
2. (b) Bräse, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp 99-166 and references therein.
3. (c) de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473-2506; Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411.
4. (c) de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473-2506; Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411.
5. (a) Voigt, K.; von Zezschwitz, P.; Rosauer, K.; Lansky, A.; Adams, A.; Reiser, O.; de Meijere, A. Eur. J. Org. Chem. 1998, 1521-1534.
6. (b) Voigt, K.; Lansky, A.; Noltemeyer, M.; de Meijere, A. Liebigs Ann. 1996, 899-911.
7. (c) Voigt, K.; Schick, U.; Meyer, F. E.; de Meijere, A. Synlett 1994,189-190.
8. (d) Lansky, A.; Reiser, O.; de Meijere, A. Synlett 1990, 405-407.
9. (a) Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133-1136.
10. (b) Heck, R. F. Org. React. 1982, 27, 345-390.
11. Plesnicar, B. In Oxidation in Organic Chemistry; Trahanovsky, W. S., Ed.; Academic Press: New York, 1978; pp 211-252.
12. (a) Levy, H.; Cope, A. C. J. Am. Chem. Soc. 1944, 66, 1684-1688.
13. (b) Bartlett, P. A. Tetrahedron 1980, 36, 2-72.
14. (c) Lutz, R. P. Chem. Rev. 1984, 84, 205-247.
15. (a) Rastetter, W. H.; Richards, T. J. J. Am. Chem. Soc. 1979, 101, 3893-3897.
16. (b) Rastetter, W. H.; Richard, T. J. J. Org. Chem. 1979, 44, 999-1001.
17. (c) Rastetter, W. H.; Richard, T. J.; Jones, N. D.; Chaney, M. O. J. Chem. Soc., Chem. Commun. 1978, 377-379.
18. (d) Detert, H.; Antony-Mayer, C.; Meier, H. Angew. Chem. 1992, 104, 755-757; Angew. Chem., Int. Ed. Engl. 1992, 31, 791-793.
19. (d) Detert, H.; Antony-Mayer, C.; Meier, H. Angew. Chem. 1992, 104, 755-757; Angew. Chem., Int. Ed. Engl. 1992, 31, 791-793.
20. (e) Quinn, C. B.; Wiseman, J. R. J. Am. Chem. Soc. 1873, 95, 1342-1343.
21. Reviews on bridgehead alkenes: (a) Keese, R. Angew. Chem. 1975, 87, 568-578; Angew. Chem., Int. Ed. Engl. 1976, 14, 528-538. (b) Köbrich, G. Angew. Chem. 1973, 85, 494-503; Angew. Chem., Int. Ed. Engl. 1973, 12, 464-473.
22. Reviews on bridgehead alkenes: (a) Keese, R. Angew. Chem. 1975, 87, 568-578; Angew. Chem., Int. Ed. Engl. 1976, 14, 528-538. (b) Köbrich, G. Angew. Chem. 1973, 85, 494-503; Angew. Chem., Int. Ed. Engl. 1973, 12, 464-473.
23. Reviews on bridgehead alkenes: (a) Keese, R. Angew. Chem. 1975, 87, 568-578; Angew. Chem., Int. Ed. Engl. 1976, 14, 528-538. (b) Köbrich, G. Angew. Chem. 1973, 85, 494-503; Angew. Chem., Int. Ed. Engl. 1973, 12, 464-473.
24. Reviews on bridgehead alkenes: (a) Keese, R. Angew. Chem. 1975, 87, 568-578; Angew. Chem., Int. Ed. Engl. 1976, 14, 528-538. (b) Köbrich, G. Angew. Chem. 1973, 85, 494-503; Angew. Chem., Int. Ed. Engl. 1973, 12, 464-473.
25. For computational studies of the relative stabilities of bridgehead alkenes, see: (a) Maier, W. F.; Schleyer, P. v. R. J. Am. Chem. Soc. 1981, 103, 1891-1900. (b) McEven, A. B.; Schleyer, P. v. R. J. Am. Chem. Soc. 1986, 108, 3951-3960. (c) Warner, P.; Peacock, S. Tetrahedron Lett. 1983, 24, 4169-4172.
26. For computational studies of the relative stabilities of bridgehead alkenes, see: (a) Maier, W. F.; Schleyer, P. v. R. J. Am. Chem. Soc. 1981, 103, 1891-1900. (b) McEven, A. B.; Schleyer, P. v. R. J. Am. Chem. Soc. 1986, 108, 3951-3960. (c) Warner, P.; Peacock, S. Tetrahedron Lett. 1983, 24, 4169-4172.
27. For computational studies of the relative stabilities of bridgehead alkenes, see: (a) Maier, W. F.; Schleyer, P. v. R. J. Am. Chem. Soc. 1981, 103, 1891-1900. (b) McEven, A. B.; Schleyer, P. v. R. J. Am. Chem. Soc. 1986, 108, 3951-3960. (c) Warner, P.; Peacock, S. Tetrahedron Lett. 1983, 24, 4169-4172.
28. (a) Shea, K. J.; Greeley, A. C.; Nguyen, S.; Beauchamp, P. D.; Aue, D. H.; Witzeman, J. S. J. Am. Chem. Soc. 1986, 108, 5901-5908.
29. (b) Shea, K. J. In Strain and its Implication in Organic Chemistry; de Meijere, A., Blechert, S., Eds.; Kluwer Academic Publishers: Dordrecht, 1989; pp 133-142.
30. Simple 1,2-monosubstituted 1,2-dialkenyloxiranes have been rearranged to 4,5-dihydrooxepines: (a) Chou, W.-N.; White, J. B. Tetrahedron Lett. 1991, 32, 157-160. (b) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975-3977. (c) Sütbeyaz, Y.; Secen, H.; Balci, M. J. Org. Chem. 1988, 53, 2312-2317. (d) Balci, M.; Sütbeyaz, Y. Tetrahedron Lett. 1983, 24, 4135-4138. (e) Pommelet, J. C.; Manisse, N.; Chuche, J. Tetrahedron 1972, 28, 3929-3941. (f) Stogryn, E. L.; Gianni, M. H.; Passannante, A. J. J. Org. Chem. 1964, 29, 1275-1276.
31. Simple 1,2-monosubstituted 1,2-dialkenyloxiranes have been rearranged to 4,5-dihydrooxepines: (a) Chou, W.-N.; White, J. B. Tetrahedron Lett. 1991, 32, 157-160. (b) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975-3977. (c) Sütbeyaz, Y.; Secen, H.; Balci, M. J. Org. Chem. 1988, 53, 2312-2317. (d) Balci, M.; Sütbeyaz, Y. Tetrahedron Lett. 1983, 24, 4135-4138. (e) Pommelet, J. C.; Manisse, N.; Chuche, J. Tetrahedron 1972, 28, 3929-3941. (f) Stogryn, E. L.; Gianni, M. H.; Passannante, A. J. J. Org. Chem. 1964, 29, 1275-1276.
32. Simple 1,2-monosubstituted 1,2-dialkenyloxiranes have been rearranged to 4,5-dihydrooxepines: (a) Chou, W.-N.; White, J. B. Tetrahedron Lett. 1991, 32, 157-160. (b) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975-3977. (c) Sütbeyaz, Y.; Secen, H.; Balci, M. J. Org. Chem. 1988, 53, 2312-2317. (d) Balci, M.; Sütbeyaz, Y. Tetrahedron Lett. 1983, 24, 4135-4138. (e) Pommelet, J. C.; Manisse, N.; Chuche, J. Tetrahedron 1972, 28, 3929-3941. (f) Stogryn, E. L.; Gianni, M. H.; Passannante, A. J. J. Org. Chem. 1964, 29, 1275-1276.
33. Simple 1,2-monosubstituted 1,2-dialkenyloxiranes have been rearranged to 4,5-dihydrooxepines: (a) Chou, W.-N.; White, J. B. Tetrahedron Lett. 1991, 32, 157-160. (b) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975-3977. (c) Sütbeyaz, Y.; Secen, H.; Balci, M. J. Org. Chem. 1988, 53, 2312-2317. (d) Balci, M.; Sütbeyaz, Y. Tetrahedron Lett. 1983, 24, 4135-4138. (e) Pommelet, J. C.; Manisse, N.; Chuche, J. Tetrahedron 1972, 28, 3929-3941. (f) Stogryn, E. L.; Gianni, M. H.; Passannante, A. J. J. Org. Chem. 1964, 29, 1275-1276.
34. Simple 1,2-monosubstituted 1,2-dialkenyloxiranes have been rearranged to 4,5-dihydrooxepines: (a) Chou, W.-N.; White, J. B. Tetrahedron Lett. 1991, 32, 157-160. (b) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975-3977. (c) Sütbeyaz, Y.; Secen, H.; Balci, M. J. Org. Chem. 1988, 53, 2312-2317. (d) Balci, M.; Sütbeyaz, Y. Tetrahedron Lett. 1983, 24, 4135-4138. (e) Pommelet, J. C.; Manisse, N.; Chuche, J. Tetrahedron 1972, 28, 3929-3941. (f) Stogryn, E. L.; Gianni, M. H.; Passannante, A. J. J. Org. Chem. 1964, 29, 1275-1276.
35. Simple 1,2-monosubstituted 1,2-dialkenyloxiranes have been rearranged to 4,5-dihydrooxepines: (a) Chou, W.-N.; White, J. B. Tetrahedron Lett. 1991, 32, 157-160. (b) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975-3977. (c) Sütbeyaz, Y.; Secen, H.; Balci, M. J. Org. Chem. 1988, 53, 2312-2317. (d) Balci, M.; Sütbeyaz, Y. Tetrahedron Lett. 1983, 24, 4135-4138. (e) Pommelet, J. C.; Manisse, N.; Chuche, J. Tetrahedron 1972, 28, 3929-3941. (f) Stogryn, E. L.; Gianni, M. H.; Passannante, A. J. J. Org. Chem. 1964, 29, 1275-1276.
36. (a) Faulkner, D. J. Nat. Prod. Rep. 1984, 1, 251-284.
37. (b) Faulkner, D. J. Nat. Prod. Rep. 1984, 1, 551-590.
38. (c) Faulkner, D. J. Nat. Prod. Rep. 1986, 3, 1-33.
39. (d) Faulkner, D. J. Nat. Prod. Rep. 1988, 5, 613-663.
40. Reviews: (a) Vogel, E.; Günther, H. Angew. Chem. 1967, 79, 429-446; Angew. Chem., Int. Ed. Engl. 1967, 6, 385-401. (b) Shirwaiker, G. S.; Bhatt, M. V. Adv. Heterocycl. Chem. 1984, 37, 67-165. (c) Tochtermann, W.; Olsson, G. Chem. Rev. 1989, 89, 1203-1214.
41. Reviews: (a) Vogel, E.; Günther, H. Angew. Chem. 1967, 79, 429-446; Angew. Chem., Int. Ed. Engl. 1967, 6, 385-401. (b) Shirwaiker, G. S.; Bhatt, M. V. Adv. Heterocycl. Chem. 1984, 37, 67-165. (c) Tochtermann, W.; Olsson, G. Chem. Rev. 1989, 89, 1203-1214.
42. Reviews: (a) Vogel, E.; Günther, H. Angew. Chem. 1967, 79, 429-446; Angew. Chem., Int. Ed. Engl. 1967, 6, 385-401. (b) Shirwaiker, G. S.; Bhatt, M. V. Adv. Heterocycl. Chem. 1984, 37, 67-165. (c) Tochtermann, W.; Olsson, G. Chem. Rev. 1989, 89, 1203-1214.
43. Reviews: (a) Vogel, E.; Günther, H. Angew. Chem. 1967, 79, 429-446; Angew. Chem., Int. Ed. Engl. 1967, 6, 385-401. (b) Shirwaiker, G. S.; Bhatt, M. V. Adv. Heterocycl. Chem. 1984, 37, 67-165. (c) Tochtermann, W.; Olsson, G. Chem. Rev. 1989, 89, 1203-1214.
44. Pearson, A. J.; Hsu, S.-Y. J. Org. Chem. 1986, 51, 2505-2511.
45. (a) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201.
46. (b) Adam, W.; Curci, B.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211.
47. (c) Baumstark, A. L.; Vasques, P. C. J. Org. Chem. 1988, 54, 3437-3479.
48. (d) Adam, W.; Hadjiarapoglou, L.; Nettler, B. Tetrahedron Lett. 1990, 31, 331-334.
49. (e) Adam, W.; Hadjiarapoglou, L.; Smerz, A. Chem. Ber. 1991, 124, 227-232.
50. (a) Ballini, R.; Marcantoni, E.; Petrini, M. Tetrahedron Lett. 1992, 33, 4835-4838.
51. (b) Emmons, W. D.; Pagano, A. S. J. Am. Chem. Soc. 1966, 77, 89-92.
52. The authors have deposited atomic coordinates for 8a with the Cambridge Crystallographic Data Centre as no. CCDC-115082. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.
53. (a) Zuccarello, F.; Buemi, G.; Favini, G. J. Mol. Struct. 1971, 8, 459-470.
54. (b) Allinger, N. L.; Sprague, J. T. J. Am. Chem. Soc. 1972, 94, 5734-5747.
55. (a) Matsumoto, K.; Uchida, T. Synthesis 1986, 1-26.
56. (b) Isaccs, N. S. Liquid-Phase High-Pressure Chemistry; Wiley: New York, 1981.
57. (c) le Noble, W. J. Chem. Unserer Zeit 1983, 17, 152-162.
58. Smith, J. G. Synthesis 1984, 629-656.
59. Brown, J. M.; Golding, B. T.; Stofko, J. J. J. Chem. Soc., Chem. Commun. 1973, 319-320.
60. Analytical data for 12b and 13b: Hillard, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1977, 99, 4058-4069.